63: The Secret Weapon to Success is No Longer a Secret with Tony Stubblebine from Coach.me

What Do Steve Jobs and Michael Jordan Have in Common? The Tony Stubblebine Story

Tony Stubblebine was not one of those 22-year-old tech startup CEOs, wearing a hoodie and distributing profane business cards. He got his start as a sharp programmer, working alongside people like Ev Williams and Biz Stone, and has been steadily climbing his way up the ladder since.

The path to becoming a successful CEO involved a lot of growth and personal development for him, almost like an athlete in training. One thing he could have used much earlier is a good coach.

“I didn’t get my first coach until it was way too late. Why didn’t I have an exec coach grooming me to be an executive, to be a CEO?”

That concept drives his current venture, Coach.me, a web and mobile app that connects users to coaches for anything from dieting to career productivity, along with simple goal and progress tracking. Coach.me spun off from goal-setting software Lift—backed by Ev Williams’ Obvious Ventures—and in its first year has matched thousands of users to personal coaches suited to their goals.

“When I pull back the curtain on someone that is successful, turns out that they had some crazy unique access to a coach that no one had access to,” Stubblebine says, noting the extremely high cost of most executive coaches. His company is based on the idea that, when it comes to business especially, more people should have that kind of guidance, and it should happen before they find success and wealth, not after.

Career Ladder

In Stubblebine’s early days, he was a programmer, and a darn good one. He was part of the launch team for personal finance company Wesabe, and director of engineering for Odeo, the podcasting platform that eventually pivoted to become Twitter (he’s Twitter user #6).

Over the years, he had basically worked his way up from individual contributor on a project, to a managing role, and then like so many us, decided it was time to start his own thing. Being a software guy, that initially meant building stuff and trying to sell it to people, getting by mostly with a few big customers who hired Stubblebine almost like a consultant.

Eventually, that turned into his first startup CrowdVine, which was a custom social media platform for any subset of people. This was back in the MySpace days, when modern social networks were still taking shape, and CrowdVine became popular among conference hosts as a way to allow attendees to get to know each other and interact.

CrowdVine has a story similar to many bootstrapped startups: “The first three or four years are just brutally hard.” For three years, while living in the Bay Area, he filed less than $25,000 in annual income.

But things got better, and they got easier. The company became profitable, and he was able to delegate more, working less on the company and splitting his time between San Francisco and New York. He was on easy street.

“I just hated it. I wanted to work on something. I wanted to work hard.”

Stubblebine came to two realizations. First, he was surprised to discover that he doesn’t really like leisure. Second, he realized that he wasn’t that interested in his company.

“Basically, for three years I went to work every day with one thought, which was, ‘I will not let this fail,’” he says. “And then once I made it work, I was left thinking, ‘Why on Earth did I build software for conferences? This is not my life’s work at all.’”

Around this time, he came around to the idea that the thing he really cares about is what he calls elite performance. A sports fanatic, Stubblebine likes to use athletes as an example, but the subject matter is mostly irrelevant.

“What habits, what skills, what insights, what talent do you need to be an elite performer in any field?”

Upping His Game

In late 2010, Ev Williams had stepped down from Twitter, and Stubblebine decided not long after that it might be a good time to invite his old friend and former boss to coffee. He showed Williams a prototype of what would become Lift, a stripped-down app that would help users set goals and stick to them. Stubblebine basically wanted to gamify life, and Williams was into the idea.

But Stubblebine was done with bootstrapping, and now he had his first investor. Soon he had gathered backers that included the likes of Tim Ferriss and Tony Robbins, but the venture capital just wasn’t following. He knew entrepreneurship was a tough game, but the feedback his team was hearing from a handful of VCs was brutal.

“Team looks great, product idea seems great, but Tony seems a little soft to be a CEO,” he recalls. Stubblebine was devastated. He figured he was missing some kind of Donald Trump-like brashness or killer instinct, and it was going to sink his company.

By that point, Stubblebine had hired an executive coach, so he asked for some coaching.

“He said, ‘Let me tell you the truth here. People are perceiving you as soft, because you are soft.’ I was like, oh my god it just gets worse and worse!”

But then his coach helped him come to grips with the problem, helping him to understand that, since he had gotten by in his career largely on smarts and his skill as an engineer, he had avoided a lot of interpersonal conflicts over the years.

This was a revelation for him, and helped him to cultivate his own version of strength, one that doesn’t involve brashness or Steve Jobs-like tyranny (it’s worth noting here that Stubblebine comes across as a genuinely friendly, thoughtful guy). Instead, he started to train himself to be more grounded over time, practicing meditation and getting better at articulating and standing firm in his beliefs.

He distinctly remembers a later meeting with more venture capitalists, grilling him on his product, and realizing he was totally unfazed. Lift ended up securing funding.

“That’s a message I like to get out to all founders, is hey, however good you are today, you could be a lot better tomorrow, so don’t worry about it.”

A Coach for Anyone and Anything

Stubblebine’s revelatory experience is not an uncommon one when working with a good coach, but it is one that very few people have access to, due to the sky-high cost of most executive coaches. It is a multi-billion-dollar industry.

This isn’t coaching as in athletic teams, but rather hiring someone to support and drive you in personal, physical, or business endeavors. Many of the most successful people in history have had someone standing just behind them, out of the spotlight, nudging them in the right direction. Steve Jobs had Bill Campbell, the executive coach who has also advised other CEOs like Jeff Bezos. Even Michael Jordan had Tim Grover, his own personal trainer who he and other basketball legends have sworn by.

As Lift was finding moderate-but-plateauing success, Stubblebine and his team were increasingly convinced that the human presence of a coach was the missing element in the mix.

“We saw almost this unfair advantage that a handful of people in the world have, and that unfair advantage is a coach,” Stubblebine says. “We call coaching the secret weapon of elite performers.”

These days, especially, there are endless sources of knowledge and education to call upon, but success really comes down to what you do with it.

“If you read Tim Ferriss’ book, you learned a ton. But then what did you do the day after you read his book? What were you doing 10 days after you read his book? That’s the role of the coach.”

So Coach.me was born out of Lift as a way to more evenly distribute this resource, by making hundreds of coaches accessible to browse online, rating them based on past experiences, and pricing them on a sliding scale. The app still has the clean interface and simple goal-setting features of Lift, but the emphasis is now much more on the people involved. Users can hire coaches for saving money, fitness, productivity, cooking, even dental hygiene. They charge as little as $15 a week, communicating online or over the phone.

Stubblebine is noticeably enthusiastic about his company, and says he draws a lot of reassurance these days knowing that, if nothing else, he’s helping people perform better in life.

When it comes to his own performance, he can see how far he’s come, but knows he is still a work in progress. He sometimes thinks of Steve Jobs, now worshipped by the startup community, who had to work at it for some 20 years before he was the Jobs we all know now. “That guy was a CEO for a really long time. … By the time he got to Apple the second time around, he was a really great CEO, but he put in a lot of hours.”

Stubblebine’s been at it for seven years now. Things are going pretty well these days, but he reminds himself that he has a lot of growth ahead. “That’s the only healthy way to look at this job.”

Tony Stubblebine’s Top 3 Insights for Entrepreneurs

Don’t feel like you have to be a jerk to get ahead. He works with lots of nice, genuine people. “Ev is a great person. When you only experience entrepreneurs through the news, it’s easy to think that they’re all like Donald Trump. Maybe even Donald Trump is really nice. … The entrepreneurs I know are just really good people. And almost the better they are as people, the better they are at attracting a team around them.”

Meditate. We hear it again and again, but he has gained so much from regular mindfulness meditation. It can be spiritual, but it doesn’t have to be. “The people I run into meditate because they want to find a way to train their brain, and it’s the most generalizable way to arrive at work strong, focused, and present.”

Successful people in entrepreneurship are heavily focused on quality of the product, much more than you would expect. “I’m just shocked with the level of detail on the product and product experience side.” They realize the importance of word of mouth after the sale, so they are relentlessly working to make it great.

Key Takeaways

A full breakdown of all the elements that make up a great leader and CEO

The secrets to utilizing meditation in order to stay grounded and tackle any and all challenges

Why you don’t need to be a jerk, and there’s nothing wrong with being the ‘nice guy’

The process of building a great product that drives social change

How to bring out that ‘elite performance’ mindset from yourself and achieve it

Full Transcript of Podcast with Tony Stubblebine

Nathan: Hey, guys. Hope you’re having an epic day. Welcome to the “Foundr Podcast.” My name is Nathan Chan, and I am coming to you live from Melbourne, Australia, and I am your host of the “Foundr Podcast.” I’m really excited about today’s guest. His name is Tony Stubblebine, and he’s the founder of Coach.me.

Now, Coach.me was actually…it was originally an app called Lift, and it was, I guess, I don’t know how to explain, but Tony kind of merged what was Lift into Coach.me. And I’m loving what these guys are doing. It’s a really, really cool service. And Tony shares so much goal with us around mentorship, coaching, why it’s important, why you need it, and his challenges as a startup founder.

Now, Tony is a big time dude out of Silicon Valley. He knows quite a few influential entrepreneurs. He’s worked at Odeo, O’Reilly Media, which are some very, very big time startups at Silicon Valley. So yeah, he’s a very, very smart guy. He’s hanging out with some very, very smart founders and entrepreneurs, and he’s a super smart guy himself. There’s so much to take away from this interview, but I’m just, let’s just jump into it guys. I’m not gonna ramble on, let’s just do this.

I hope you enjoy this episode. If you are enjoying these podcast episodes, please do leave us a review. It helps more than you can imagine. It would be very, very, very appreciated if you leave us a review in iTunes. And also, don’t forget to tell you friends. I forgot that one, but yeah, don’t forget to tell your friends. Speak soon, now is time for the show.

Thank you so much for taking the time. The first question I ask every one of our guests is, how did you get your job?

Tony: Hey. You know, people talk about career ladders, and I think what’s funny about my job is the CEO job is the one job that you can just give yourself. Anyone can just say, “Oh, I’m a CEO now, and I’m running this company. I’m the CEO of my lemonade stand.” So that’s kind of tongue in cheek, but it is how I got the job. Is that I was tired of working for other people, and I wanted to do my own thing, and so one day I said, well, hey… You know, I’m a programmer originally, I know how to build software, why don’t I build some software and start selling it to people? And, you know, predictably, I was terrible at it. Most people didn’t want my software, and the people that did get it, were kind of frustrated by how well it worked, or how well it did not work.

But over time, I just, you know, kept building things and building things for other people.

Nathan: So you’re doing consulting?

Tony: You know, that’s interesting. I’m curious like how you approached that first company. So this company I’m doing right now, Coach.me, I would consider it the third product that I’ve founded. The first one had no investors. This one has really big name investors.

So that first one, you’re like on your own. Nobody believes in you. You don’t have a lot of experience. The way that I funded it was, first, I just took a couple of months to build stuff on my own, and then I found a couple of customers, and then I found one really big customer that would almost pay me as a consultant. But it was based on the software, so it was like kind of white labeling a software often turns into a big consulting project as you add features to that software for them.

So for the first two years, that first company, the company was called CrowdVine. For the first two years, half of our revenue was coming from just a handful of really big clients, who were basically treating us as consultants.

What other strategies do people use for that first company? Because I feel like that’s actually a really good one.

Nathan: Yeah, yeah. No, that’s a really good question. Like right now, you know, Foundr is my first company, and we’re only running it for two and a half years. It is very difficult to work out how to get your first customers, especially when you don’t know the spice, and you’ve got to make yourself an influencer, you’ve got to make yourself an expert, you’ve got to make yourself an authority, you’ve got to build that trust.

So I’m curious, with this first company, how did you get first customers, or your first big customers, that you speak of? And then, I guess, what happened to it, and how did you wind up? Like let’s find out how you wound up doing Coach.me.

Tony: Yeah. So I built a version, in the CrowdVine days, I built a version. The idea that I had was that I was going to build a way for anyone to create their own social network. That’s actually almost pre Facebook. More people were thinking about My Space back then.

Nathan: Oh, yeah. That was like 10 years ago.

Tony: Yeah. I mean, it doesn’t feel like a while ago, 2007, I think, was when I launched it. And the idea that you could kind of create a mini Facebook for your company, or for your conference, or something like that. And the way that I got first customers, I mean, I just, I almost locked into it. Everyone I met, I asked them, “Hey, would you wanna use this for…?” and then I would make up whatever reason I thought was most appropriate to them.

And I kind of stumbled into using it for conferences, and the use case of the conference was actually really powerful. Most people go to a conference and they want to network, but they don’t know anyone there, and so you kind of get all the attendees that becomes this hyperactive attendee directory, basically. And then when you show up having seen everyone’s faces and connected with a lot of people, and then when you walk into the cocktail hour, you’re like, “Oh, I recognize that person. I wanna talk to them about this.” Or you know, you just know immediately who you wanna talk to, and so it’s a lot more social.

Nathan: Oh, well.

Tony: So we did that. We, you know, we got a couple of trial conference customers, and then tried to sell it to more and more companies, customers. And then along the side, we had, you know, one or two customers that were like trying to create a social network for scientists, or a social network for programmers, and so we were doing that contract work on the side.

So I thought, like ever a lot of friends that work on just any contracting project in order to fund the thing that they really love doing, the kind of product that they’re trying to build, and I really like combining that contracting with the product, because it just, like the product did get better along the way, and that’s how we were able to make some money. We did that, that company was alive for four years, and it followed this trajectory that I’ve seen a lot of loose track companies take, which is that the first three or four years are just brutally hard.

I feel like no one really understands what brutally hard means, so I just, like I started to say this is what I made, how much money I made. So I was living in the Bay Area, and I think for three years in a row, I’ve reported less than $25,000 to the IRS.

Nathan: Wow.

Tony: You know, my salary at Google would be like $250,000, you know, 10 times that, at least. I bet then that’s probably about what it would have been. So I was really leaving a lot of money on the table, but I was doing something that I loved, and I wanted to learn how to be a founder.

And then this is the key though, is that that period where you’re grinding it out, eventually, you become profitable. And once you’re profitable, then you’re on easy street, because you can hire people to do the jobs for you. You don’t have to work as hard. Like all of the strain of the first couple of years goes away. So in year four, I was working on it maybe a day a week. I had a team of a couple of people that were running the whole thing for me, and I had enough money that I was not then splitting my time between San Francisco and New York. So a pretty comfortable lifestyle business at that point.

But then I had to face this real tough question, which I wouldn’t have predicted was gonna be tough, which is do a like leisure? You know, when you’re an entrepreneur, I think a lot of us dream, like we wanna be able to set our own hours. And here I had like actually achieved it. I had plenty of time to myself, and I just hated it. And I was like, I really didn’t, I wanted to work on something. I wanted to work hard, does that make sense to you? I mean, can you imagine just retiring and sitting on the beach for years on end?

Nathan: Tony, you don’t understand how much the story resonates with me, man. Because one of the reasons I started Foundr is because I read, you know, Tim Ferriss’ book, “The Four Hour Work Week,” who I know you know well. He’s one of the investors in Coach.me.

Tony: Yes.

Nathan: And that kind of got me excited. And then I built this business, which is Foundr, and it became a lifestyle business, and I could work whenever I want. But then after that you just, you want to build so much more. Like it’s just not enough, you know what I mean?

Tony: Right.

Nathan: And so I totally get it. This resonates with me really, really also. Please keep going.

Tony: I think you really, as a founder, you really get addicted to the impact that you have on the world. I mean, you have this opportunity to have this really big impact. We were talking before we started recording, about, so we talked about the successes or the failures.

So for me, I actually kind of almost looked at this company as a huge failure. And this is the lesson that I wish other people would learn, or that I could teach other people, which is in that fourth year, you know, I realized two things about myself. One, I wanna work. So then I’m looking at this company and it’s 100% selling software to conferences at that point, and I had asked myself, “Do I want to reinvest my time in this company?” Essentially, do I wanna become the world’s expert in conferences? And start the answer was resoundingly, “No.” I have no interest in that.

And so now I’m looking at that four year period, where I mean look, there’s a ton of person growth, I’m a completely different person after that than I was going into it. But I’m looking at that four year period and saying I basically, for three years, I went to work every day with one thought, which was I will not let this fail. Essentially, my pride was just wrapped up in making it work. And then once I made it work, I was just left thinking, “Why on earth did I build software for conferences? This is not my life’s work at all.”

And so that was the real reevaluation that led me towards Coach.me, is that the thing that I care about is elite performance. And honestly, I could care less what genre we’re talking about. I’m a sports fan, I’m a fan of entrepreneurs, but I got, you know, I could get hooked in a show like “Project Runway,” which is about what it takes to be a great fashion designer. To me, all of those things are the exact same thing. What habits, what skills, what insights, what talent do you need, to be an elite performer in any field?

For a long time, I’ve known like that is the thing I’m most interested in. That’s what I’m reading about all the time. And so I looked at CrowdVine and I was like, man, I have to walk away from this and do something that’s really authentic to me. And that’s what I decided to do, and that’s I think how we met, is you used the first product that I did in that space, which was a goal tracking community called Lift. Did you use that back when we first launched?

Nathan: Yes. Since I read the “Four Hour Work Week,” it took me a while to start my own business, which is Foundr. And I saw Tim, he did a post on it. This is actually feedback, yeah, he did a post on it and I downloaded it straight away.

Tony: He is one of the best investors of all time. I love being involved with him. He is so helpful at every level. I mean, one, he gave us money, but he also gave great business advice, and then he helped to, about once a year we’ll collaborate on some projects together and he will drive a ton of traffic and be really fun and interesting and just a big win-win for both of us.

So that first company, CrowdVine, that was bootstrapped, meaning it had no investors. I’ve been in Silicon Valley. I’ve worked for startups, I have all these connections here. And felt like I should at least consider getting investors the second time around. So I started playing with this idea of gamefying your life. I thought well, like imagine if there was no inertia, if you said, my goal is to run every day, and then you ran every day, there is no negotiation with yourself, there’s no struggle to it. You just did the work. So I wanted to try and gamefy my life that way.

I had a prototype of something that became Lift, and I went out to coffee with a friend. My friend Evan Williams, who used to be my boss, but who is most well known for being the founder of Twitter, and now Medium, and way back in the day, the founder of Blogger. So basically, one of the best serial entrepreneurs in tech.

He had just left Twitter, and I don’t know what happened. It’s like I’m the only person that invited him to coffee, but I did. We went out for coffee, I showed him this prototype and he’s like, “You know what, we should do this together. Let me invest and I’ll help design the first version with you.” So that’s what we did. That’s where Lift came from.

And it was, I remember this kind of an amazing group of people that came together at the start. We mentioned Tim Ferriss, Tony Robbins was also an investor.

Tony: Yeah. It is kind of who’s who of productivity. I think the only person that we couldn’t get that we wanted was like Oprah. People kept saying, “Who do you wanna intro to?” and I’d say, “I wanna intro to Oprah.”

Nathan: I got a story about that, man.

Tony: Have you met her?

Nathan: I haven’t met, but her team contacted us to do an interview. And I was really keen to interview her, but you know, she had time very, very, as you can imagine and I kind of tried to wangle, because she does a lot of stuff with Deepak show prop, and I was like, “Okay, we can do like a joint, you know, front cover with Deepak and Oprah.” And they said yes to it, but then we only got Deepak at the end of it.

Tony: What does she know about creating a media empire? She has been just so effective on that. So anyways, we started this company Lift, and it was like semi-successful, but not breakout successful. And so at some point we really just had to face, you know, come to grips with that so well, listen, like we’re in the right ballpark, but we’re not in the ballpark. We have to change.

But this is where going back to lessons learned, I know what my life’s work is now, and so I’m not like, I would never go from goal tracking to photo sharing. Like a lot of entrepreneurs are just throwing spaghetti on the wall, trying to see what sticks. And I’m like, I know every day what, when I wake up, I’m gonna be working on self-improvement and some passion. I just, I find that very reassuring just because the job is so stressful, because you don’t know the outcome. You don’t know if your company is going to go out of business.

You know, especially for us at Lift, we were 100% dependent on our investors, so we weren’t making any money. How do you feel? Do you talk much about the stress of being a founder?

Nathan: Yeah, I do. And I really try and touch on it a lot when I’m speaking to other founders and doing interviews, because I think it’s such, like nobody really talks, people do talk about the dark side of entrepreneurship, but not as much as they should. I couldn’t even imagine, you know, with 100% bootstraps just, wow, and being profitable. You have pretty much since the early days, but we’re not playing a nearly a big scale as you are.

But I’m really curious, how did that feel to know that, you know, you went from your first company to being a profitable startup? And you are now with Lift, you weren’t really making any money, how did that feel? Like for me, I’m driven by, I guess the revenue stuff. That really excites me.

Of course the impact, but for me the impact is a reflection all of the revenue as well, if you know what I mean. So how did that feel?

Tony: Bad.

Nathan: Because it must be so tough. I don’t know how you could go through that, like that would be really hard for me.

Tony: I’ll elaborate. Yeah, well first of all, it’s very common out here, right? A lot of consumer-focused startups don’t have any revenue for a really long time. And I just find that revenue is grounding. I feel more stable if there’s revenue, because one, you get to call your own shots.

Nathan: That’s right.

Tony: But two, you know where the value is. And that, I really like. Now at Coach.me, we do have revenue. We’re getting paid for changing people’s lives, there is no better feeling in the world. And it’s very clear when the checks come in that we’ve done good work. So yeah, absolutely. I think that’s the main thing. For me, that’s the struggle, is without revenue, I just feel at a loss often. So I would say I’m thrilled to be back to running a revenue focused company.

I probably won’t ever, hopefully, this is my last company, and that’s always the oath, but regardless, I don’t, I can’t really imagine starting another company where revenue was not a key part of it.

I’m curious, when you were starting, was there like really tough feedback that you got?

Nathan: Yeah, I remember when I was showing the magazine to people, because you know, Foundr is a digital magazine on the App Store, the Google Play Store, I was showing it and people were just like, you know, what you’re doing can’t be done. You know, would Richard Branson wanna speak to you? You know, kind of things like that.

Yeah, we got we got some bad feedback, but at the same time, Tony, I think for me, and in my world, it’s a lot different to how you guys think. I just came back from the States and I’m starting to capture, you know, what it means to think 10 or 100X bigger, because when I started, I started Foundr while I was working my full time job. And I built it up to replace my income, you know, and I thought that was what I was gonna do, like run this lifestyle business.

But then I realized very quickly that it’s so much more than that. And you know, yeah, look I could take an investment, I could grow it even faster, but I normally just take it one step at a time, one step at a time. So like, you know, I’m working on wanting to build a $10 million company, and I know you guys you think $100 million, you know, half a billion dollar company, billion dollar company, and that’s just so beyond me. Does that answer your question?

Tony: You have to pass through $10 million to get to $100 million. I think that’s the, right? Like, that’s the thing. You have to remember that regardless of where you think you’re going, you do have to get through today. And, you know, for me today was an interview, some product work and three partnership meetings. Those three partnerships aren’t going to make or break the company, but they’re important steps towards being that much bigger company.

You know, this is, like it’s very much a mindfullness practice, right? And I think it’s super hard for an entrepreneur to just, how can you live in the moment, and reevaluate the long term trajectory, but how can you live in the moment?

I was thinking, you know, we were talking about the stress of a company that’s not quite working. I remember at one point, and this is kind of a transition for a little bit of coaching that I’ve received along the way. I remember at one point we were trying to raise money from DC, so we had, you know, we had great angel investors, including Tony Robbins and Tim Ferriss, and really great team of people that were well known and well respected in the industry.

We went to these venture capitalists, and like seven or eight in a row said basically the same thing, never to my face, but always to the person that introduced me. They said, “Team looks great, product idea seems great, but Tony seems a little soft to be a CEO.”

Nathan: Wow.

Tony: And I’m like, “Oh.”

Nathan: That’s a bit harsh, ouch.

Tony: I mean, it’s very much, like it’s a personal attack. I was ready for, “This product will never work. You don’t have enough traction.” That would have made a lot of sense to me, but just like I personally, am not good enough for this company, was super harsh.

One of the things I like about my career is that my career is the career ladder of a founder. Like, I started as an individual contributor, then I became a manager, then I worked for other startups, then I put step to start ups, then I got investors and did a traditional venture back start up. And along the way, I didn’t always look like a CEO. I wasn’t like Mark Zuckerberg at 22. But I just kept proving to myself that if you do the work, the personal development work, you absolutely can turn yourself into a, you know, a great manager, a great leader, a great entrepreneur. And certainly, that’s something I’m working towards every day. But that, assuming that path that there was a lot of really big improvements.

So when I got that feedback from the VCs, I mean, first of all I was like, I practically died when I heard that, because what it meant was that the company might just go out of business, if we don’t get investment, we’re gonna die. And then two, I was worried. I mean, legit worried, that I wouldn’t be able to develop a killer instinct, is how I thought of it. So I went to my coach and I said, “You know, I keep getting this feedback, what’s going on?” and he goes, “Tony, let me tell you the truth here, people are perceiving you as soft because you are soft.” And I was like, “Oh my God, it just gets worse and worse.” Right?

Nathan: Yes.

Tony: And he actually had this way of framing it that really I felt like there’s a pattern I see over and over again. He said, “Look, a lot of times, the thing that got you here becomes the thing that’s holding you back.” So the way that I got through in my career is being really smart, really knowing, really technical, really good at my job, really collaborative. But it never required me to be really firm, or to really deal with other people that were particularly strong willed, so I just like I never really had to fight for anything, because I could just outwork everyone.

So I asked my coach, his name is Jonathan, I asked him, “Well, you know, can I develop a killer instinct?” I think of myself as a nice guy, and I thought what the VCs were looking for was someone like Donald Trump, someone to just come in and be ultra-brash and like…

Nathan: Shock.

Tony: Yeah, shock and awe, right?

Nathan: Yeah.

Tony: Thankfully, and this is where, one of the things a coach can really do is help you reframe the way you’re thinking into a healthier way. And what we talked a lot about was, what does strength look like for me? And for me, the easiest thing is, I’m just generally very grounded, and one thing that I do like working on is just knowing what my philosophies are, what it is that I think and believe.

And so the more that I worked on being grounded, which of mostly through meditation, and the more I worked on articulating, here are the things that I believe, that I’m firm on, the more that I became, not so much brash, but free of weakness. And that’s what I think of whenever I meet someone who is like way deep into mindfulness, is they just, you can’t bluff them, because they don’t get emotional. I mean, technically, they get emotional but they are so aware of those emotions that they never, you know, waver because of them.

And so now I’m talking to VC, when we actually did raise money, the end step of it was that I was in a room full of seven VCs, that kind of the partner meeting, so all of the partners at this one firm were grilling me about what we were gonna do with the product. And at that point, I’d had months of training and meditation and also really how to be stronger leader, and I was completely unfazed in that meeting.

That was a really big jump between apparently these early venture capitalist meetings where I think I was just like so wishy washy, if they asked me a hard question I probably got really nervous. So I mean, that’s the message I’d like to get out to all founders, it’s hey, you know, however good you are today, you could be a lot better tomorrow. So don’t worry about it.

Nathan: It’s all mastery, man.

Tony: Yeah, it’s like the, sort of the 10,000 hours then. I mean, people up here really worship Steve Jobs. One of the things I think about Steve Jobs is, like that guy was a CEO for a really long time.

Nathan: Oh, yeah.

Tony: The Steve Jobs we know at Apple was a shitty… I can say shitty on this podcast, right?

Nathan: Of course.

Tony: Actually about Steve Jobs. His first gig at Apple was terrible. Not terrible, I mean, but it wasn’t great. You know, most people thought he was kind of a crappy manager. Then eventually, he got pushed out. And then it felt like his second stand and next step was so successful. I mean, basically, Apple had to buy him out. And it’s really only after 20 years of doing it he came back and really I think, knew what he stood for and could articulate it, and knew how to select for and knew his management team.

So yeah, by the time he got Apple the second time around, he was a really great CEO. But he put in a lot of hours, so to his credit, but also he had a lot of opportunity, and so I think of myself, I’m like, “I’ve been a CEO for seven years. I’m just getting started. I have a ton more growth to do.” And I think that’s really the only healthy way to look at this job.

Nathan: Yeah. No, that’s a really good point. It’s all about, you know, just appreciating the journey and just knowing you’re putting in the time towards mastery, right?

Tony: Right. Do you use a coach at all?

Nathan: That’s a really good question, and that’s why I’m really excited. Another reason I’m really excited speak to you, Tony. Because, you know, I was saying to a friend, like I have a lot of mentors and I’m very blessed, this amazing network that I’ve built up in a short period of time since starting Foundr. I always, if I have a massive problem, I go around the room to like 10 different people, all my mentors, friends, you name it. And then I seem to just nod it out, and I always, you know, for the most part, go in the right direction.

I said to my friend though, “I think I need a coach to take it to the next level.” Like this network and the mentors I have and stuff, it will only get me so far. And he’s like, “Yeah, I think you’re right.” He’s like, “I reckon I’m gonna get a coach soon too.” I’ve never had one somebody that is committed, fully, fully committed that we check in, you know, every couple of weeks or once a month, and be like, “This is what you need to do next. This is where you’re at. This is…”

Because with I found with mentors, or friends, or advisors of sorts, you can just check in with them when you need, but it’s not really an ongoing scheduled check-up and that person’s really, really keeping you accountable. That’s why I see how you’ve gone from that segue between Lift and now Coach, because there’s more accountability from the person who saw it, and pushing you in the right direction. Would you call it a pivot? Is that how the pivot came about to Coach.me?

Tony: Yeah, definitely, I think we would call it pivot. At the beginning of this year, I could actually almost call it, I would call it the third thing, you know. First I built CrowdVine, then I built Lift, then I built Coach.me. It just happens that Coach.me is in the same company as Lift, so we used a lot of the Lift assets in order to build it.

Nathan: Yes.

Tony: But a lot of it is like it’s a different family and teams than the original Lift team and it’s just, in a lot of ways it’s so different but we just find it’s healthier to think of it as a brand new thing where, you know, we’re eight month into a brand new thing, but in the same mission of Lift of, you know, how do we help people perform at their best? And absolutely, well, we looked at what it took. We saw almost this unfair advantage that a few handful of people in the world have. That unfair advantage is their coach.

And so we call coaching the secret weapon of elite performers because everywhere I looked, you know, when I pull back the curtain on someone who is really successful, turns out they had some crazy, unique access to a coach that no one else had access to. So you can say like Michael Jordan was one of the first basketball players to really get into weight training, and his coach Tim Grover, that’s his personal coach that Michael Jordan paid out of pocket, not the coach that the Chicago Bulls gave to him. Not part of the Chicago Bulls coaching staff. This is like on the side he had a personal trainer helping to keep him strong and healthy for a really long career.

And even looking further than that, a lot of times you hear all these stories about athletes, because I think there’s a lot of pressure on that space, but you know, what I would say is special about let’s say Serena Williams, is like has won the last four tennis opens in a row and when this goes live, might have won five in a row. You know, what’s special about her is the coaching that her dad did. He did all sorts of weird stuff that your normal coach doesn’t do. I just heard the other day he felt like they were going to get, that Serena and her sister were gonna get a lot of cat calls from the crowd, so he actually busted people to stand around their practice and scream and curse them while they practiced, which… I just like [crosstalk] right?

Nathan: Yeah.

Tony: You know, like screaming racist things at them, like the whole thing. So those two kids, when they hit their professional circuit, they were ready for anything. And going back even more, you know, like what’s special about Tiger Woods as well? Tiger Woods had a dad who is probably the world’s best coach of three year-old golfers in the world. And so, yeah, Tiger put in a lot of work, and you know, simply loved golf for a long time, but he had this huge advantage that weighed ahead of everyone else. He was getting great golf training early on, and that just sort of reinforced itself.

And so once you’re the best 10 year-old golfer in the world, the best coach of 10 year olds is going to ask to coach you, and just going on and on and on. And of course, he turned into a top golfer. I mean, in hindsight, you wish he’d had some relationship coach, maybe, but…

Nathan: Yeah, that’s right.

Tony: So but this is, I don’t even know if people know of him and the golfer family, but his marriage sort of disintegrated after it came out that he was sleeping with dozens of hookers, I mean, really like crazy personal life.

But the achievement on the sports side is legit, and that came from coaching. You know, we talk about Steve Jobs, even he has a really famous coach, this guy…

Nathan: Oh, really?

Tony: This guy, Bill Campbell, used to be a football coach for Columbia University in New York, and then became an executive coach for a lot of people out here in the Bay Area. Worked with Steve Jobs. I just met Phil Knight, executive coach recently former founder and CEO of, former CEO now of Nike. But I like the athletic framework because athletes assume they’re going to have a coach.

You know, the more that I meet the elite athletes, I always thought, wow, these people are very athletic. That’s why they’re athletes.

Nathan: Yeah.

Tony: But when I meet them, the defining characteristic of the professional athletes is that if you present them with an advantage and say, “Hey, if you do this, you’ll have an advantage,” they just do it. They do zero hesitations. It’s shocking. And you say like, “Oh, hey, if you wear this Band-Aid on your nose, you’ll be able to breathe better,” and boom, they’re all doing it, right? They have no hesitation about that.

You know when I saw that really white strip, I was like oh, that’s kind of cool. Maybe I should use it. I even got some for free, and I never work them. I think that’s really, like that ended up being the difference in a lot of ways. It’s like every advantage that you can offer, they’ll take it. And I think if you’re in business, you should treat it the exact same way, as if you’re an athlete.

You know, the exact coaching of business is totally backwards. I always say, I joke, I didn’t get my first coach until it was way too late. Like why didn’t I have an exec coach when I was 22 grooming me to be an executive, to be a CEO? I would be way more prepared if I had started much earlier. And the way the exec coaching mostly works is that you don’t get your first coach until you’re already a CEO, and you’re already a successful CEO. Because those coaches are expensive, normally.

So like when I have in CrowdVine, I wasn’t gonna hire an executive coach. I was only making $25,000 a year, where am I gonna afford $400 a session coaching? This is one of our goals of coaching, is can we make coaching accessible to everyone? Because there are so many great coaches out there, they’re just hard to find. And if you do find them, they’re often way too accessible. So we have these amazing coaches that would work with you for as little as $15 a week.

Nathan: Yeah, wow. Tony, I have to say, you know, after this conversation I’m jumping on Coach.me, and I’m getting myself a coach. You know, how you used that Michael Jordan story, when me and my friend were talking about should we need a coachm, or do we need a coach, or do I need a coach? He was saying, you know, with Michael Jordan, if the coach told him to do it, he’d do it. And sometimes, it’s good to get that direction, but I have to ask, there’s something I’m dying to ask you, do you always have to do what your coach tells you to do? And then, how do you know if that person is a good coach? Because, you know, that could be a very dangerous position where the coach tells you what to do, and is not the right move, or…you know what I mean?

Tony: Right. I mean, we’ve all had that experience with advisors, right? It’s like just because the advice works for them, doesn’t mean it’s gonna work for you.

Nathan: That’s right.

Tony: So, a couple of things, in business coaching, there’s much more of an emphasis on facilitating. So a lot of times, the business coach, you’re presenting a problem to the business coach, the business coach is helping you frame it in a way where you play a really big role in coming up with the solution.

So, you know, like you don’t come to your business coach and say, “Okay, here’s the performance review on this person, should I fire them or not?” and then they’ll go, “Yes,” and that’s the end of discussion. They’re gonna say, “Well, what are your standards for keeping people? What are your options for if this person does go?” here are other things that I see other people doing at other companies. Like you just have a much, they’re much more of a partner with you, so you’re not to ever go too far of course, because you’re part of it.

I mean, when you’re in middle school, right, like I had a middle school basketball coach. I was 12 years old, 11 years old. Of course, I was gonna do what my coach told me to do, I didn’t know anything about the world. Like you’re a CEO right now, but you’re not gonna get bluffed by someone. You’re much more worldly. You know a ton about what works and what doesn’t work in your business.

And this is actually why I think executive coaching works so well, is you, basically you end up with two high level people, really having a high level strategic conversation about the business and the organization that you’re running. So I never really worry about the wrong advice.

There is this question of quality. Before Coach.me, was a great question because the answer was, “You have no idea.” You have no idea who’s good and who’s bad, all you can work on is referrals. Like, do you have a friend who knows a coach, who worked with a coach and liked them? And even then, that person usually only worked with one coach, so you don’t know, you might know the coach is okay, but you don’t know if they’re the best, you don’t know if the next coach you talk to might be better.

So that’s a problem, and here’s how we solved it at Coach.me, is we look at retention. So we’ve had, I think we’ve had about 600 coaches now who’ve had paying clients. And it turns out how long the client stays with them is an amazing predictor of how good the coach is. And we, you know, we back this up by actually talking to the clients and talking to the coaches and looking at the record of the coaching.

That retention rate for our top coaches is three times longer than our average coach, so if you ever search for a coach on our system, the ones at the top of the search results, those are the best coaches. We ranked them based on how successful their clients are. And you could never do that before, but we have a complete record of every coaching interaction down to what people said to each other, and for that reason, it’s actually really easy for us to rank them. But what’s surprising about the ranking is how broad that range is.

So a bad coach, the clients cancel him right away, a mediocre coach, the clients tend to work out one problem and then stop with the coaching. And then a great coach, you work out one problem and then you love the coach and you look for other problems to work on together. And those coaches build really long term relationships with their clients.

Nathan: I see.

Tony: Does that put you at ease at all?

Nathan: Yeah. Yeah, definitely. Another question I have, and this is something that I think I saw in an article when I read about you a while back. I think it was on “Tech Crunch,” maybe, is it is very affordable, like super affordable. How does that work from the coach’s standpoint if they are a great coach? How does that make it in the best interest of them? Because for me, I’d be happy to pay $200 a session, or $300, $400, you know what I mean?

Tony: Right.

Nathan: Like $15 a week is very cheap, Tony. Like, it’s nothing man.

Tony: I know. Well, first of all, there’s absolutely, if you want to, you can pay more. So if this is really bothering anyone who is listening, please, we’ll find a way to give you even more value for more money.

You know, we pitch the price based on testing. We’ve picked a price that would get the most coaches to the most people, and then we double checked that against whether or not we could provide great coaching at that price. But what happened there is sort of just obviously, more people buy at 15 than at 20, and a lot more people buy it at 15 than at 50. But the other thing that’s sort of the good news is that there’s a ton of people in the world who want to provide coaching. If you’re a coach in San Francisco or New York, which is where I split my time between those two cities, yeah, you absolutely have to be charging $100, $200 or $400 an hour, just to live in those places.

One of our top coaches is in rural Texas. She is the CEO of a 250 person organization, but wants to give back. Has learned a ton in that CEO role, but wants to help other people. We have another type coach in Ohio, top coach in South Africa right now. I think the economics are just different. Once you do this in scale and you’re actually able to rank the coaches, we’re able to spot lots and lots of top coaches who…And that’s certainly enough for us to keep those current price points.

So I agree, it’s a great deal. You’re getting $100 in coaching for $15. So I mean, the value that we’re able to get you incredible for that price point.

Nathan: Yeah, it’s a deal, man. I think of your platform a little bit like Clarity, but for coaches and more of an ongoing support type system.

Tony: Sure.

Nathan: Is that a good way to kind of say it’s in the same kind of the area?

Tony: Absolutely. I feel like if I’m talking to a tech insider, that we’ll talk about the freelance economy, and you know, there’s actually a range. So on the one hand, some startups, it’s like you have a service end of it, which is Uber. You know, I heard about a house cleaning startup where the people that were getting sent to your house, some of them were literally homeless. That’s one end.

And then the other end is these coaches who are these high level professionals, you know, former CEOs and CIOs and CTOs. So we call that the elite end of the freelancer economy. Obviously, Clarity is in there. I call Upwork, which used to be known as Elance and Odesk, so that they’re in there. They can be in there too, the professional end.

You know, the thing about Clarity, which I think is true of a lot of the self-improvement world is that a lot of people know how to give the advice, not that many people know how to help you follow the advice. And so, after your call on Clarity, how are going to turn that into something that you do every day? That’s what a coach is for.

Nathan: Yeah. [crosstalk].

Tony: Literally check in with you every day. And, you know, that’s not on Clarity, I mean, if you read Tim Ferriss’s book, you learn to talk. But then what did you do the day after you read his book? What were you doing 10 days after you read his book? That’s the role of the coach.

So in a lot of ways, the coach is like 90% of the value. You don’t get value from reading the book, you get value from putting it into practice. And, you know, that’s why we’re so gang row on coaching.

Nathan: Yeah. Look, you’ve made it an absolute no-brainer, I’ve got to get a coach.

Tony: That’s awesome.

Nathan: You’ve answered my question, so yeah, I’ll go and jump on Coach.me. Look, we have to work towards wrapping up, Tony. You were definitely right that we would go overtime. I could talk to you all day, man, I’m really enjoying this conversation. A couple of things, let’s talk a little bit more on the dark side of entrepreneurship. Take us back to one moment that’s been one of your toughest moments. I know you said you lived on a salary of $25,000. That would be really tough. Take us back to a real moment that just was so tough, where you thought to yourself of giving it all up. Or have you ever thought of giving up?

Tony: Well, I mean, this is absolutely one of my hacks for not giving up, was to work on something that was meaningful. So I feel like even if I lost everyone’s money, every day that I came to work, we helped tens and hundreds and millions of people now, make their lives better. So like I was never going to feel guilty about the money we lost, because the net impact on the world was so good.

I’m thinking about one moment in particular. It’s just, you know, this company, Coach.me is really a second swing, but within the same company. So, not everyone wanted to go along with it. I mean, most people had signed up for one thing with the Lift company kind of mission. You know, we put a lot of work into it, and it just didn’t work. And I think people felt like, you know, we failed and it was time to move on.

So I went to our investors and I said, “Hey, I think there’s something they do here as more of a platform. I wanna do it, can you guys help us out? Can you give us a little bit more money?” So basically, I pitched them on a small, inside round. That’s the money that we still have in the bank right now, but then we’re just edging up on profitable, which is a huge success for us.

So as I’m pitching these investors, at the same time, my co-founder was thinking that he didn’t wanna continue with that. It just was kind of, the opportunity cost was so great. This wasn’t even necessarily what he wanted to do. Like Coach.me is not that much of a tech company, and then less about the building product and more about staffing that product. But he didn’t tell me, and so I pitched to our investors, they said yes, but they said verily, who is on my board, he said, “Listen, the partners said yes, but they all said, you know, this is like, it’s not going well. There’s no more money after this. This is the last chance, you’ve got to figure it out.” But they said, “Yes.”

So basically, the day after I stepped up my back and said, all right, this is great. The terms are great, can you wire the money? My co-founder came to me and said, “I don’t wanna continue.” Like literally, right before the money got wired to me. I would just say that that was probably the lowest moment for me, because like we’ve gone from I’ve saved the company to as positive the value of money.

I mean, first of all, I had to tell him. I couldn’t just sit on the news and wait for the money to get wired, because so much of our money comes from my friend Evan Williams. But being my boss, back in the day, had been the Twitter CEO, was on our board, helped me design this, I would never hide something from him. Honestly, I probably wouldn’t hide it from any partner, you know, any of my investors, although I know some founders would. But that’s just like there is zero chance that I was gonna sit on this news, so I knew I had to call them.

And I was positive they would pull out, because that’s what I would do. I mean, absolutely, if I was the investor and I got that news, I would have pulled out. So I texted Bishan [SP]. I forget what I said, but he, after we ended up talking, he was like, “When I saw your text I basically thought, either you have cancer or your co-founder quit.” Like there’s just like only two things that it could. Thankfully, I mean, I just had really good investors, because they said, “Well, look, this is really bad news for you. Your friend bumped you out, you’re going to have to work harder, but it doesn’t change the opportunity. And we believe in you, let’s just move forward with it.”

So they didn’t change the terms, nothing. They just wired the money the next day and we went on. But I mean, having those conversations with my board, that, “Look, you know, my co-founders is leaving, it’s going to be tough,” it was so scary. And turned out to be anything. Turns out…

So, you know, and Coach Evans, my co-founder, a lot of ways he did the right for him. And I can’t fault him. I think his reasoning was right on. And actually, he saw things in a lot of ways more clearly than I did. He tried to convince me that he wouldn’t be a good fit because we weren’t really that technical of a company any more. And I said, “No, no, no we will need you.” But the reality is if I had 10 people to hire tomorrow, eight of them would be up in business and content side, for sure.

Nathan: Yeah, okay. So it was…

Tony: As he predicted.

Nathan: Yeah. So it was a blessing in disguise.

Tony: Yeah. I mean, I like him so much, I hate to call it a blessing. But we made you, and you know, in fact, it was good for everyone. I think the investors, they got their money back, Coach.me feels like a huge thing. Coaching as at right now is a nine billion dollar industry, which is crazy because like how would you even get a coach? Is how I feel.

Nathan: Yeah, I agree with you. That is so true. Like that is what me and my friend were going through. You only go through referrals.

Tony: Right. It’s just such a mass industry, so I think about it as an industry that’s just artificially small. And so when we talk about a lower price point, what we’re talking about is making that nine billion dollar industry a $90 billion industry. There should be 10 times more people with coaches. We just have to make them a lot more accessible, and that’s what we’re trying to do right now.

Nathan: Awesome. Well, look Tony, I have one last question, and that is you’re very blessed. Your network is amazing. You mentioned that Evan is a really good friends of yours and you’ve had an amazing network, you’re deep within the Bay Area. What are the top three things that you’ve noticed amongst all of the super successful entrepreneurs in your network? And, you know, what are the top three things that the audience needs to be focusing on?

Tony: Well, one, I know a lot more people that are nice, or you know, they’re real people. Evan is a great person. So I think when you only experience entrepreneurs through the news, it’s easy to think that they’re all like Donald Trump, right? Maybe even Donald Trump is really nice behind the scenes. But there’s just that public persona is bullshit. The entrepreneurs that I know are just really, really good people, almost the better they are as people, the better they are at attracting a team around them. I think Evan is a great example of that.

Two, I just feel more and more about meditation as a performance practice. It’s not about spirituality. Or it could be about spirituality, if that’s what you want, but the people I run into, meditate because they wanna find a way to train their brain. And it’s the most generalizable way to arrive at work strong, focuses and present.

Third, it’s a good one, sort of counter-intuitively, well maybe this is actually intuitive, but I just find that people who are successful are really focused on the quality of the product, way more that you would think is logical. Because, you know, it’s like in some ways it’s like if people will buy it, then that should be good enough.

I think that there’s probably a lot more word of mouth going on in the world than you realize. So, you know, you might think, “Oh, my channel is this. As long as I’m on store shelves at Best Buy, I’m in good shape,” right? Actually, it’s the person who bought it once and then told their friends, that’s really what’s driving it in a lot of the sales.

So I’m just shocked by the level of detail on the product and product experience side that people put it into, I otherwise wouldn’t really see. So you know, even like Tim Ferriss, his whole thing about how to build an audience is not to post a Facebook 12 times a day. I’ve seen articles that say the ideal number of times that you should post to Twitter or Facebook is 10 or 12. And I’m thinking, no, it’s crazy. What you wanna do is create content that is incredibly high quality.

So they’ll put out these 30-page articles that are just like almost mini books, right? And he’s giving that stuff away for free. I’ve worked with him on written pieces before, and his attention to detail is through the roof. I mean, not like the grammar, the logic, like if you make a claim, you have to back it up. And then just also the kind of the sales psychology of it, like how does it connect with the person? I mean, he is amazing at that. And that’s true for practically every successful person I’ve run into.

Nathan: Yeah. Well, that’s some great insight. Yeah. So look, anyone listening to this, definitely check out the interview we did with the founder of Headspace, which is a brilliant guided meditation app.

I just wanted to touch on that, you know, nice guy thing, because the late Dave Goldberg, I interviewed him in the early days, and one of the best pieces of advice that he shared was there’s a lot of assholes out there, if you’re nice to people, would go along way.

Tony: Right.

Nathan: That’s really sat well with me, because I consider myself a nice guy too, Tony.

Tony: Great.

Nathan: Yeah. But look, thank you so much for taking the time. This has been an awesome conversation. Where is the best place to find you?

Tony: Oh, well obviously, that will come to the website, coach.me, or download the app, coach.me. Actually, everything we talked about, so it’s right there on the homepage. That’s where people should go.